Hydrochloric Acid → N-acetyl-N-ethyl-2-(acetylthio)acetamide

HRID 1855763Notes

Reaction equation

HRID 1855763 reaction equation
[C:1]([NH:4][C:5](=[O:11])[CH2:6][S:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].[H-].[Na+].[H][H].[CH2:16](I)[CH3:17].Cl>O.CCOCC.C(O)(=O)C.CN(C)C=O>[C:1]([N:4]([CH2:16][CH3:17])[C:5](=[O:11])[CH2:6][S:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12837856N-acetyl-2-(acetylthio)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 20540298N-acetyl-N-ethyl-2-(acetylthio)acetamide

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 11 g. (0.063 mole) of N-acetyl-2-(acetylthio)acetamide in 75 ml. of dry dimethylformamide was cooled to -30° C. and there was then added 3.02 g. (0.063 mole) of 50% sodium hydride. The reaction mixture was aged until hydrogen evolution ceased. There was then added 5.1 ml. (0.063 mole) of ethyl iodide after cooling the reaction mixture to -40° C., after which the reaction mixture was allowed to come to room temperature and age overnight. A precipitate formed. There was next added 5 ml. of acetic acid, then 100 ml. of ether, followed by 30 ml. of 2.5 N hydrochloric acid and 70 ml. of water. The ether layer was separated and the water layer was increased to about 400 ml. with water, after which it was extracted three times with 100 ml. of ether. The ether extract was dried over magnesium sulfate and concentrated to an oil of 7.2 g. Composition of the product was verified by NMR and mass spectrometry.

Workup

  1. additionthere was then added 3.02 g
  2. additionThere was then added 5.1 ml
  3. customto come to room temperature
  4. customage overnight
  5. customA precipitate formed
  6. additionThere was next added 5 ml
  7. customThe ether layer was separated
  8. temperaturethe water layer was increased to about 400 ml
  9. extractionwith water, after which it was extracted three times with 100 ml
  10. extractionThe ether extract
  11. dry with materialwas dried over magnesium sulfate
  12. concentrationconcentrated to an oil of 7.2 g

Sources & evidence

ORD record
ord-1566035279774fea89fb0f2a6d057bef
Source dataset
uspto-grants-1980_08
Patent number
US04216160

Reaction notes

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